Triethylamine → HCID 58522032, compound

HRID 2390277Notes

Reaction equation

HRID 2390277 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].I[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.C(N(CC)CC)C.CCOC(C)=O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 108934-IodoanilineHCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 58522032HCID 58522032, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (4-chloro-2-ethynyl-phenoxy)-acetic acid tert-butyl ester (Intermediate 3; 800 mg; 3.00 mmol), 4-iodoaniline (788 mg; 3.60 mmol) and dichlorobis(triphenylphosphine)palladium(II) (526 mg; 0.75 mmol) in anhydrous THF (20 mL) was treated with cuprous iodide (29 mg; 0.15 mmol), then the mixture was degassed with N2 for 10 minutes, then treated with triethylamine (5.0 ml; 36 mmol). The mixture was stirred for 18 hours at RT, then EtOAc and water were added, the phases separated and the organic phase was dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc to give the title compound.

Workup

  1. customthe mixture was degassed with N2 for 10 minutes
  2. customthe phases separated
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by flash column chromatography (silica)
  6. washeluting with cyclohexane containing
  7. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-75934e49f18b450ea105c3af22114dfd
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

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